Ammonia → 3,5-DI-Tert-butyl-4-hydroxybenzylamine

HRID 1430362Notes

Reaction equation

HRID 1430362 reaction equation
C([NH:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1)=O.N>O1CCOCC1.Cl.O>[C:11]([C:9]1[CH:10]=[C:5]([CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]=1[OH:15])[CH2:4][NH2:3])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 13438362N-(3,5-di-tert-butyl-4-hydroxybenzyl)formamide

Product 1

HCID 6010783,5-DI-Tert-butyl-4-hydroxybenzylamineYield 97%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

9.81 g (37.3 mmol) N-formyl-3,5-di-tert.butyl-4-hydroxybenzyl-amine was dissolved in 24 mL dioxane and 7.2 mL concentrated hydrochloric acid. The mixture was heated to reflux for one hour. The mixture was allowed to cool down to room temperature and diluted with 50 mL water. The mixture was made alkaline, using a 10% ammonia solution. 3,5-di-tert.butyl-4-hydroxybenzyl amine precipitated from the medium, was isolated by filtration and dried. 8.5 g (97%) of 3,5-di-tert.butyl-4-hydroxybenzyl amine was isolated (m.p.: 159-9° C.). 3,5-di-tert.butyl-4-hydroxybenzyl amine has a tendency to lose ammonia upon heating, forming the corresponding di- and tribenzyl derivatives.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for one hour
  3. custom3,5-di-tert.butyl-4-hydroxybenzyl amine precipitated from the medium
  4. customwas isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-19163426984d4b618c81c40bfeb34d3b
Source dataset
uspto-grants-2015_01
Patent number
US08940811B2

Reaction notes

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